Mr Herriman's Day Off
by jakbossmaster
Summary: During the years that Mr. Herriman has worked for Foster's Home for Imaginary Friends, he finds that every now and then that he needs some rest from the rest of the house even from Madame Foster herself, but ever rarely takes a break. It's not until Frankie convinces him to take his day off & "relax for a change." (Keep in mind that this is basically Male/Solo. Rated M people)


Mr. Herriman was doing his usual morning work like any other day of the week, except it was supposed to be his day off. Despite barely having anything to work on, he tried to keep his mind busy on something rather than "other things." He heard a voice coming from outside his office and knew who it was.

Frankie walked into his office making small talk to who ever she was talking to.

"Alright, I look into it later. Look, I gotta get this done before you-know-who gets on my butt about-" She cut herself off when she saw Mr. Herriman. "AH M-Mr. Herriman! W-what are you doing here? Isn't it your day off?" Obviously trying to change the subject before things can get worse for her.

"Well, I'm just trying to get some extra work done." There was a bit of awkward silence.

"Wait "extra work?" I thought you got everything done 3 days ago. What kind of overtime could you be doing that's worth losing your day off for?" Frankie said. "I thought I could just double check that if any other appoints to adopt imaginary friends were on the correct dates, Miss. Francies." "You do that every day when you finish work early and have an extra day off." Frankie instantly replied, "You should really take the day off Mr. Herriman. It's not healthy for you to overwork." "B-but there's-" Mr. Herriman tried to come up with a reason to keep working but was cut off. "No buts sir! Your going take this day off to relax, and have some fun. Grandma would say the same thing if she were down here." Herriman took in what she just said, and it would be true either way. She proceeded to shove Herriman out of the office and say, "Listen, I'll take care of whatever needs to be done around the house and office today. You go relax for a change." Herriman gave a short sigh and said, "Alright, if you say so Miss. Fancies…" "Ok good. Just don't me see you in this office trying to work again, or I'll hide your documents." Herriman quickly snapped his head "I already agreed to "relaxing for a change" haven't I? No need to go to extreme lengths!" Frankie gave small smirk, "Alright sir, go on and enjoy your day off!" She closed the door to Herriman's office and left him outside.

Herriman was left there standing out in the main entrance of the house, left with only his thoughts. He honestly didn't know what he wanted to do. There was only one thought he's been having, and it's the one thing he was trying to get off his mind for so long. He shook his head and looked at the time and it was only about 8:15 AM, still relatively early. "I guess I'll take a walk around the house for a good while."

He went up several floors to explore the hallways to see what everyone's up too. Mostly everyone was doing good for the most part. He did make small talk with a few others, and even decided to check up on Bloo and the gang to make sure everything was ok and not causing another episode. Surprisingly enough, the gang, including Mac, were all watching a marathon of their favorite show, supposively leading up to a big final episode of the season.

Herriman was quickly getting bored of walking around, and that "thought" was getting closer. He was unsure if even wanted to attempt it, but it was quickly repressed with something else on his

mind. "Maybe I should redecorate my room…" he muttered to himself. It was unlike him to think about his room, but he's mostly been neglecting it. He only ever goes into his room to sleep, and rarely does anything else. It's probably gathering up dust at this point. His room was near the top the of house where all the important members of the house live. Most of the VIP rooms are far apart from each others so nothing much can be heard between rooms.

He entered his room and took in what he saw. It looked too simple. It didn't really appeal too much to him. He wanted his room to have a good structure so he can sleep, get to his clothes, work on things- "That's it!" Herriman yelled to himself. "I'll just arrange a work area for me so I can continue working!" He hopped his way towards the storage closet in his room and looked for what even can be used as a desk, or at least build one.

Luckily enough, there were tools and a box for DIY desk. "Uh? I guess I ordered one a long time ago and forgot about it." He must've been so absorbed into doing work he forgot about it. He picked up the box and moved it the middle of the room and went back to the closet to grab the box of tools on the shelf. "Uh?" He shuffled through his closet and find a reticular box with a note attached.

"We all have those moments. Use this to help you relax."

"P.S. Make sure you do this hands-free for the best results! :P"

Herriman grabbed the box and sat on his bed and proceeded to open it. What he found inside was what pushed that one "thought" into full view. It was an 8 in. multifuction dildo. His face turned bright red at the sight of it, and was slightly turned on at the thought of what he could do with it. He shook his head and grabbed an instruction manual that was inside the box as well.

It read: "Deluxe Multifunction Dildo. This product is here to give all the pleasure you need in many ways. This dildo by standard comes with: special cum lube, auto pump functions, and our newly added stance that allows you to stick it on any surfaces!"

The description of the manual made this dildo sound like heaven, and even turned Herriman on even more, but there was one problem: He's never used a dildo before, and was afraid to even try it. Admittedly, he is getting tired of the usual routine, and because of how long it been since his last real "relaxing day off" he thought it would be a nice change of pace. He was both nervous and excited at the same time. Nervous because if he were to go through with it, he have to be careful not to attract any attention (And not leave too much of a mess). Before he did anything, he went to the bathroom and grabbed a towel and headed straight back to room. He locked the door, and moved back to his bed.

He was getting even more excited while he was prepping himself for his dildo. So excited that he was already leaking pre. He's package is a 7 ½, practically normal for himself with some above average balls. His butt is nice, round and fluffy too. He grabbed the dildo to learn what it can do. There's a cable that was linked to a controller that has all the functions listed in the manual. He thought he would start slow before moving on any of the functions. The dildo itself is designed to look more look an human penis with a diameter of 2 in which is rather large, with a ballsack near the base, presumingly holding the cum lube. The ballsack actually moves too!

Herriman took the dildo and placed it on the floor next to his bed. He wanted to go slow and get used to it. Before he got into position he took another moment and examined the dildo once again. He was getting extremely horny just by the thought and sight of shoving it up his ass, but still nervous. His pre was leaking, a lot. It's about enough to lube up the dildo. He took off his gloves and held his dick to grab as much pre as he could and cover up the dildo as much as possible. To him, it looked amazing...A dildo covered in pre-cum…

Herriman began to drool at the sight of the dildo, he had the natural instinct to lick it and so he did. He felt disgusted in himself, but found it incredibly sexy. He continued to lick up more of the pre on the dildo and realized that he was leaking again. He repeated the same process and earlier and did it again, but this time sucking on it. The salty flavor and action of giving a dildo a blowjob felt amazing. Herriman was just too horny to resist. He held the dildo in one hand sucking it, and the other cupping the tip of his dick to gather whatever pre was still leaking. For several minutes he continue to do what he was doing, but now he felt ready. He licked his lips to get whatever pre was still on him, and cover up the dildo with a handful of pre that's about enough to give him an easy entrance.

He propped himself with his back against the bed. With one hand, he held the dildo in place to make sure he doesn't miss. He took a deep breath and lowered his butt onto the pre covered dildo. The tip breaks the entrance, giving Herriman a small gasp. He slowly proceeds to lower himself to get more of what he wants. Each inch felt like hell and pleasure at the same time. The new feeling is so weird and good. Herriman took a short break around 4 in. He needed to adjust to the foreign body that was now in his butt.

It was weird how he enjoyed this so much. He was never into men and the thought never occurred to him. He heard that a lot of straight guys try anal, and even went as far to give women the role of dominance. Herriman may have found his new kink, but he would have to go through with it, and finish it first.

He continue to slowly take it all in slightly faster speed. 5in, 6in, 7in...and finally hit the base. Herriman let out a deep gasp of pleasure. He sat there taking it in once more. He felt the sticky warmth of his pre that was now in him. He only felt harder because of this. He proceeded to move back up, letting the pleasure build up. He stopped near the tip, and slide back down slowly. His gasp quickly turned to soft moans, "Oohhh...Yeeeesss…" He continued this slow pace for a few minutes, taking it all in.

About 10 minutes in, he decided to pick up the speed. He was moving a normal speed that won't hurt him. Herriman's pre was all over the floor underneath and over most of the tip of his dick. His cock was bouncing up and down somewhat because of Herriman's new current speed. His pants of pleasure was getting a little louder. His small tail was beginning to wang, and his foot was even thumbing a little.

About another good 10 minutes pass and his legs began to get tired from making himself bounce up and down for so long. He sat onto the dildo at it's full length and panted for a few second, then grabbed the controller. He looked at the settings and saw "Auto-Pump" with 4 speed settings. He lifted himself off his dildo and moved it next to the wall. He covered up the dildo once more with as much pre as he could and stuck the dildo on the wall. He also grabbed a pillow off his bed and placed it on the ground close to him. He positioned himself onto all four with his pillow for him rest on if needed. Herriman posed his fluffy butt in front of the dildo, and made sure the tip was at the entrance. He grabbed the controller and put "Auto-Pump" speed at 1. The dildo penetrated Herriman's butt slowly, giving him pleasure once more after the short break. It pulled out, and pushed back in, pulled out, and in.

The speed was too slow, but pleasurable. He gave himself a second to adjust to the new sensation of an automatic pound. He then turned on the Auto-Pump to speed 2, and instantly the speed was back to the way he had it earlier. The moans came back, and being in the new position he's in, it felt better, buts it not like he didn't enjoy the other one earlier. He just felt more comfortable. He took this position to his advantage and laid his head down on the pillow in front of him and just took it. He quickly adjusted to his position, and speed of his dildo and tried pushing back and forth on it. It felt great, it felt natural. He could feel the balls of his dildo hitting his butt and his own balls, lightly. His dick was swinging in the air underneath him, with pre still leaking. Herriman grabbed the box that held his dildo and placed it underneath his dick to catch his pre that he could use for later. Herriman continue to push himself in and out in rhythm with his dildo. Only great pleasure, and moaning was achieved. "Ah...ah...ah." Herriman did feel slightly tempted to jack it, but he remembered the note that came with the box, and that's what kept him going.

He grabbed the remote again and switch the speed to 2.5 (the switch is like a knob). The speed started instantly, and Herriman can feel the force of the dildo pushing in and out, and balls hitting him somewhat harder. It felt even better. His tail started to wag faster, he changed his rhythm to match the new speed, and began thumbing his foot again.

For about 15 minutes, he kept up with this speed, but he was getting tired, he needed a new position and he wanted to pick up the speed again. He turned off the Auto-Pump function and let the dildo slip out, that pull out pushed him hard. Herriman took it off the wall and once again, applied another huge load of pre splattered all over it, making it look like it might explode. He place the dildo on the wall slightly lower than before and got his back. He shuffled himself towards the dildo and stuck it in about 2 inches in. He took a sec to lay his head on his pillow and looked at himself. His dick was rock hard and felt pretty close as well. "It must be time *pant* to finish this…"

he said to himself.

Herriman grabbed the remote once more and set the speed to 3. The different in terms of speed was radically different than 2.5. The dildo hit his fluffy bottom harder, and the balls hitting his butt was harder too. It felt fantastic. The warmth and stickiness was greater too. It felt like heaven. All Herriman could do was throw his head back in pleasure, pant, and moan even louder. He could feel his body somewhat rocking back and forth, and he just wanted more of it. He kept this speed on for about 5 minutes then grabbed the remote for one more time. He set the speed to 4, it's maximum speed, and it hit harder than ever. The speed was like a real person thrusting at their top speed and ready to hit their climax. Herriman took another look at the remote and found the "Cum Lube" button and made sure to remember it.

Herriman felt like he was in true bliss. He was rocking back and forth on the floor and can feel like he about to blow. "Just a little...longer…" He felt pure pleasure, and wanted it to last. Pre was leaking all over Herriman's stomach and his butt. The warmth of it was all over. He starting cupping up as much pre as he could and started tasting it. All of this was setting him over the edge. It won't be long.

About 3 minutes pass and his moans, and pants were at it's loudest. "Ah! Ah! Fuck me! Fuck me!" Herriman said loudly. He couldn't take it much more. He began to rock back and forth in rhythm once more as fast and as hard as he could to earn his blissful moment. Each time his dildo slammed into his fluffy bottom, he just wanted more of it. It was time to finish it. Herriman took hold of the remote once more and kept it close to him. He was almost about to cum. "AH! AH! AH!" He pressed the button and the warmest cum lube flooded his fluffy butt while still pounding him hard., and this is what sent him over the edge. The combined feeling of being fucked so hard, licking his pre, using his pre as lube, and the feeling of warm cum feeling him sent him over. AHH! AHHHHH! AHHHHHH~

He came all over himself and in the air too that shot past his face. His orgasim lasted for a good minute. Once he recovered he turned the speed back down to 1 to give himself a break before getting up. He could feel the cum from his dildo still in him and leaking out as well. Even his own dick was leaking a good few ounces. He finally hit the stop button and moved away, pulling out the dildo in the process. He laid there for a minute and looked to the side to look into his vertical standing mirror. It was angled perfectly to show off the mess he created. He was sweaty, extremely red, and his butt, his chest and face were covered in cum. It really did show how pent up he really was.

Herriman got up very weakly. His legs were weak, and shaking, he could barely stand up. He grabbed the towel he set aside and cleaned up the areas that was covered in cum and sweat. After that, he unlocked his door and looked outside to see if anyone were there. Luckily, no one was. He shut the door again, locked it, and slid down it. He sat there in thought about how AMAZING that felt. It was something he had never done before and wished he found out sooner. Just the thought about being fucked harder next time he did already made him feel really hard.

"Maybe I should take the rest of the day off…" Herriman said to himself. And so he took the whole day off "relaxing" for a change...


End file.
